Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14–88% yields. Take advantage of the synthetic intermediate 7h , the key B/C rings in brazilin core could be constructed by the s...

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Published inNatural products and bioprospecting Vol. 14; no. 1; p. 29
Main Authors Hu, Xin-Ting, Cheng, Qing-Yan, Chen, Yan-Ping, Li, Kun, Yan, Cai-Xian, Li, Dashan, Shao, Li-Dong
Format Journal Article
LanguageEnglish
Published Singapore Springer Nature Singapore 01.12.2024
Springer Nature B.V
SpringerOpen
Subjects
1,3-Diarylpropene
Acids
Biomedical and Life Sciences
Bioorganic Chemistry
Brazilin
Catalytic Prins reaction
Decomposition
Food Science
Friedel-Crafts reaction
Hydroxylation
Hydroxymethylation/hydroxylation
Life Sciences
Logic
Medicinal Chemistry
Natural products
Original
Original Article
Pharmacology/Toxicology
Plant Biochemistry
Plant Sciences
Precious metals
Stereoselectivity
1,3-Diarylpropene
Brazilin
Catalytic Prins reaction
Hydroxymethylation/hydroxylation
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Summary:A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14–88% yields. Take advantage of the synthetic intermediate 7h , the key B/C rings in brazilin core could be constructed by the sequential of Friedel–Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel–Crafts reactions. Graphical Abstract
Bibliography:ObjectType-Article-1
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ISSN:2192-2195
2192-2209
DOI:10.1007/s13659-024-00450-2